CA2353498A1 - Methods of preparing or purifying onium hydroxides by means of electrodialysis - Google Patents
Methods of preparing or purifying onium hydroxides by means of electrodialysis Download PDFInfo
- Publication number
- CA2353498A1 CA2353498A1 CA002353498A CA2353498A CA2353498A1 CA 2353498 A1 CA2353498 A1 CA 2353498A1 CA 002353498 A CA002353498 A CA 002353498A CA 2353498 A CA2353498 A CA 2353498A CA 2353498 A1 CA2353498 A1 CA 2353498A1
- Authority
- CA
- Canada
- Prior art keywords
- electrodialysis
- membrane
- anode
- anion
- selective membrane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000909 electrodialysis Methods 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 44
- 150000004679 hydroxides Chemical class 0.000 title claims abstract description 17
- 239000012528 membrane Substances 0.000 claims abstract description 99
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 150000001450 anions Chemical class 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000012535 impurity Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000003586 protic polar solvent Substances 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- 239000000243 solution Substances 0.000 description 18
- -1 quaternary ammonium ions Chemical class 0.000 description 16
- 239000008896 Opium Substances 0.000 description 15
- 229960001027 opium Drugs 0.000 description 15
- 239000003011 anion exchange membrane Substances 0.000 description 14
- 235000011114 ammonium hydroxide Nutrition 0.000 description 12
- 125000001453 quaternary ammonium group Chemical group 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- 150000001768 cations Chemical class 0.000 description 9
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 5
- 150000004010 onium ions Chemical class 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000007848 Bronsted acid Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 229910001853 inorganic hydroxide Inorganic materials 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 2
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- BPDXQUQWFRPXQJ-UHFFFAOYSA-M 1,1-di(propan-2-yl)-4,5-dihydroimidazol-1-ium;bromide Chemical compound [Br-].CC(C)[N+]1(C(C)C)CCN=C1 BPDXQUQWFRPXQJ-UHFFFAOYSA-M 0.000 description 1
- NUKXHTILEMYWNF-UHFFFAOYSA-M 1,1-dimethylpiperidin-1-ium;bromide Chemical compound [Br-].C[N+]1(C)CCCCC1 NUKXHTILEMYWNF-UHFFFAOYSA-M 0.000 description 1
- OTYUSDYTGRXYKG-UHFFFAOYSA-M 1,1-dimethylpyrrolidin-1-ium-2-one;bromide Chemical compound [Br-].C[N+]1(C)CCCC1=O OTYUSDYTGRXYKG-UHFFFAOYSA-M 0.000 description 1
- UWWBOMDVVJGEPA-UHFFFAOYSA-N 2,2-dihydroxyethyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC(O)O UWWBOMDVVJGEPA-UHFFFAOYSA-N 0.000 description 1
- NIZJVQDOWGPBQW-UHFFFAOYSA-N 2,2-dihydroxyethyl(dimethyl)phosphanium;bromide Chemical compound [Br-].C[PH+](C)CC(O)O NIZJVQDOWGPBQW-UHFFFAOYSA-N 0.000 description 1
- XNBUZNKPVWOQHY-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)phosphanium;bromide Chemical compound [Br-].C[P+](C)(C)CCO XNBUZNKPVWOQHY-UHFFFAOYSA-M 0.000 description 1
- BUYCSRDEWLPKCP-UHFFFAOYSA-M 2-hydroxyethyl(tripropyl)azanium;chloride Chemical compound [Cl-].CCC[N+](CCC)(CCC)CCO BUYCSRDEWLPKCP-UHFFFAOYSA-M 0.000 description 1
- MSIGGUSMCUUDGY-UHFFFAOYSA-M 2-methoxyethyl(trimethyl)azanium;chloride Chemical compound [Cl-].COCC[N+](C)(C)C MSIGGUSMCUUDGY-UHFFFAOYSA-M 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- GEYBMYRBIABFTA-UHFFFAOYSA-N O-methyltyrosine Chemical compound COC1=CC=C(CC(N)C(O)=O)C=C1 GEYBMYRBIABFTA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- NVWVWSGPCYTKMR-UHFFFAOYSA-M [Cl-].C(CC)[N+](CCOC)(CCC)CCC Chemical compound [Cl-].C(CC)[N+](CCOC)(CCC)CCC NVWVWSGPCYTKMR-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000011162 ammonium carbonates Nutrition 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- VTQLZQMNJYFXIZ-UHFFFAOYSA-M benzyl(trimethyl)phosphanium;bromide Chemical compound [Br-].C[P+](C)(C)CC1=CC=CC=C1 VTQLZQMNJYFXIZ-UHFFFAOYSA-M 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CUFDHSAIDGERSH-UHFFFAOYSA-N methyl(2,2,2-trihydroxyethyl)azanium;chloride Chemical compound [Cl-].C[NH2+]CC(O)(O)O CUFDHSAIDGERSH-UHFFFAOYSA-N 0.000 description 1
- CZRYQCBUSCRLGW-UHFFFAOYSA-N methyl(2,2,2-trihydroxyethyl)phosphanium;bromide Chemical compound [Br-].C[PH2+]CC(O)(O)O CZRYQCBUSCRLGW-UHFFFAOYSA-N 0.000 description 1
- MHQIMVYNMHGQSF-UHFFFAOYSA-N methylphosphanium;bromide Chemical compound [Br-].[PH3+]C MHQIMVYNMHGQSF-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 238000003969 polarography Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- MKWYFZFMAMBPQK-UHFFFAOYSA-J sodium feredetate Chemical compound [Na+].[Fe+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O MKWYFZFMAMBPQK-UHFFFAOYSA-J 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IVCPVUGUFSYYKG-UHFFFAOYSA-M tetra(propan-2-yl)azanium;bromide Chemical compound [Br-].CC(C)[N+](C(C)C)(C(C)C)C(C)C IVCPVUGUFSYYKG-UHFFFAOYSA-M 0.000 description 1
- WALNCKJQTNNUDQ-UHFFFAOYSA-M tetra(propan-2-yl)azanium;chloride Chemical compound [Cl-].CC(C)[N+](C(C)C)(C(C)C)C(C)C WALNCKJQTNNUDQ-UHFFFAOYSA-M 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- LIXPXSXEKKHIRR-UHFFFAOYSA-M tetraethylphosphanium;bromide Chemical compound [Br-].CC[P+](CC)(CC)CC LIXPXSXEKKHIRR-UHFFFAOYSA-M 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- QBVXKDJEZKEASM-UHFFFAOYSA-M tetraoctylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QBVXKDJEZKEASM-UHFFFAOYSA-M 0.000 description 1
- FBEVECUEMUUFKM-UHFFFAOYSA-M tetrapropylazanium;chloride Chemical compound [Cl-].CCC[N+](CCC)(CCC)CCC FBEVECUEMUUFKM-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- SMGSPBKMKYMJPQ-UHFFFAOYSA-M tetrapropylphosphanium;bromide Chemical compound [Br-].CCC[P+](CCC)(CCC)CCC SMGSPBKMKYMJPQ-UHFFFAOYSA-M 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GRQVEMICAANVOS-UHFFFAOYSA-M triethyl(phenyl)phosphanium;bromide Chemical compound [Br-].CC[P+](CC)(CC)C1=CC=CC=C1 GRQVEMICAANVOS-UHFFFAOYSA-M 0.000 description 1
- MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 1
- WHAFDJWJDDPMDO-UHFFFAOYSA-N trimethyl(phenyl)phosphanium Chemical compound C[P+](C)(C)C1=CC=CC=C1 WHAFDJWJDDPMDO-UHFFFAOYSA-N 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/42—Electrodialysis; Electro-osmosis ; Electro-ultrafiltration; Membrane capacitive deionization
- B01D61/44—Ion-selective electrodialysis
- B01D61/445—Ion-selective electrodialysis with bipolar membranes; Water splitting
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Water Supply & Treatment (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Urology & Nephrology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Water Treatment By Electricity Or Magnetism (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19856376A DE19856376A1 (de) | 1998-12-07 | 1998-12-07 | Verfahren zur Herstellung oder Reinigung von Oniumhydroxiden mittels Elektrodialyse |
| DE19856376.0 | 1998-12-07 | ||
| PCT/EP1999/009515 WO2000034224A1 (de) | 1998-12-07 | 1999-12-06 | Verfahren zur herstellung oder reinigung von oniumhydroxiden mittels elektrodialyse |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2353498A1 true CA2353498A1 (en) | 2000-06-15 |
Family
ID=7890237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002353498A Abandoned CA2353498A1 (en) | 1998-12-07 | 1999-12-06 | Methods of preparing or purifying onium hydroxides by means of electrodialysis |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6527932B1 (enExample) |
| EP (1) | EP1137625B1 (enExample) |
| JP (1) | JP4233764B2 (enExample) |
| KR (1) | KR20010082325A (enExample) |
| CN (1) | CN100339355C (enExample) |
| AT (1) | ATE251110T1 (enExample) |
| AU (1) | AU770841B2 (enExample) |
| BR (1) | BR9915996A (enExample) |
| CA (1) | CA2353498A1 (enExample) |
| DE (2) | DE19856376A1 (enExample) |
| ES (1) | ES2211210T3 (enExample) |
| ID (1) | ID29240A (enExample) |
| MX (1) | MX221393B (enExample) |
| WO (1) | WO2000034224A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2369311B (en) * | 2000-11-24 | 2002-12-11 | Membrane Extraction Tech Ltd | Separating phase transfer agents |
| US6787021B2 (en) * | 2002-01-03 | 2004-09-07 | Sachem, Inc. | Purification of onium hydroxides by electrodialysis |
| WO2006114414A1 (de) * | 2005-04-26 | 2006-11-02 | Felix Böttcher Gmbh & Co. Kg | Verfahren und vorrichtung zur kontrolle und begrenzung der verkeimung in feuchtmittelkreisläufen |
| JP4736519B2 (ja) * | 2005-04-27 | 2011-07-27 | 住友化学株式会社 | 弗化４級アンモニウムの製造方法 |
| US7604724B2 (en) * | 2007-07-03 | 2009-10-20 | Aristos Energy Inc. | Method for sour gas treatment |
| EP2237855A1 (en) * | 2007-12-20 | 2010-10-13 | Paques B.V. | Process for removing sulfide from alkaline washing liquids |
| KR101144820B1 (ko) * | 2009-10-21 | 2012-05-11 | 한국에너지기술연구원 | 이산화탄소 분리 장치 및 방법 |
| CN102690206A (zh) * | 2011-03-25 | 2012-09-26 | 敏森工程有限公司 | 氢氧化四甲基铵的回收系统与方法 |
| CN102531927B (zh) * | 2011-12-28 | 2013-09-11 | 浙江工业大学 | 一种利用双极膜电渗析制备四丙基氢氧化铵的方法 |
| CN104292114B (zh) * | 2013-07-19 | 2016-05-04 | 广州众合环保工程技术服务有限公司 | 一种鎓氢氧化物的制备方法 |
| CN104593810A (zh) * | 2014-12-20 | 2015-05-06 | 中山大学 | 一种连续流生物电化学系统制备四甲基氢氧化铵的方法 |
| CN104532286B (zh) * | 2014-12-22 | 2017-12-19 | 中山大学 | 一种回收葡萄糖酸盐废水中葡萄糖酸的生物电化学方法 |
| CN106350831A (zh) * | 2016-08-26 | 2017-01-25 | 肯特催化材料股份有限公司 | 分子筛模板剂高纯度金刚烷基三甲基氢氧化铵水溶液的制备方法 |
| CN106958028B (zh) * | 2017-05-22 | 2019-05-07 | 江苏三吉利化工股份有限公司 | 一种三室两膜电解法制备高纯四丙基氢氧化铵的装置 |
| CN107652185A (zh) * | 2017-07-03 | 2018-02-02 | 杭州龙智科技有限公司 | 苄基三甲基氢氧化铵的制备装置及制备方法 |
| CN108467347A (zh) * | 2018-03-22 | 2018-08-31 | 新乡化纤股份有限公司 | 一种电解四丁基硫酸铵溶液回收四丁基氢氧化铵的方法 |
| CN108486604A (zh) * | 2018-03-26 | 2018-09-04 | 新乡化纤股份有限公司 | 一种以四丁基硫酸铵为原料制备四丁基氢氧化铵的方法 |
| CN108711632B (zh) * | 2018-04-03 | 2021-03-26 | 天朤(江苏)氢能源科技有限公司 | 一种燃料电池用阴离子交换膜及其制备方法 |
| CN109134266B (zh) * | 2018-09-21 | 2021-06-15 | 南京元亨化工科技有限公司 | 一种基于复合双极膜电解制备高纯四丙基氢氧化铵的方法 |
| CN113105500A (zh) * | 2021-04-08 | 2021-07-13 | 沈阳金久奇科技有限公司 | 电渗析法在L-α-甘磷酸胆碱生产中的纯化除盐工艺 |
| CN116571086B (zh) * | 2023-05-15 | 2025-11-25 | 北京理工大学 | 含能离子化合物的电渗析膜浓缩新方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1199991B (it) | 1983-03-17 | 1989-01-05 | Anic Spa | Procedimento per la preparazione di idrossido di ammonio quaternario mediante elettrodialisi |
| GR880100210A (el) * | 1987-04-15 | 1989-01-31 | Alusuisse | Μεθοδος για την ελατωση των ακαθαρσιων εις τα αλκαλικα διαλυματα της μεθοδου bayer |
| US5162076A (en) * | 1988-11-30 | 1992-11-10 | Allied-Signal Inc. | Method for purification of acids from materials comprising acid and salt |
| EP0572389B1 (en) * | 1991-02-01 | 1995-01-25 | The Graver Company | Separation/recovery of ammonium salts via electrodialytic water splitting |
| US5286354A (en) | 1992-11-30 | 1994-02-15 | Sachem, Inc. | Method for preparing organic and inorganic hydroxides and alkoxides by electrolysis |
| US5389211A (en) * | 1993-11-08 | 1995-02-14 | Sachem, Inc. | Method for producing high purity hydroxides and alkoxides |
| US5833832A (en) * | 1996-08-30 | 1998-11-10 | Sachem, Inc. | Preparation of onium hydroxides in an electrochemical cell |
| US5709790A (en) | 1996-10-03 | 1998-01-20 | Sachem, Inc. | Electrochemical process for purifying hydroxide compounds |
| US5753097A (en) | 1996-10-03 | 1998-05-19 | Sachem, Inc. | Process for purifying hydroxide compounds |
| US5853555A (en) | 1997-04-03 | 1998-12-29 | Sachem, Inc. | Synthesis of onium hydroxides from onium salts |
| US5904823A (en) | 1997-04-10 | 1999-05-18 | Sachem, Inc. | Methods of purifying hydroxylamine solutions and converting hydroxylamine salts to hydroxylamine |
-
1998
- 1998-12-07 DE DE19856376A patent/DE19856376A1/de not_active Withdrawn
-
1999
- 1999-12-06 AU AU19706/00A patent/AU770841B2/en not_active Ceased
- 1999-12-06 EP EP99963393A patent/EP1137625B1/de not_active Expired - Lifetime
- 1999-12-06 DE DE59907231T patent/DE59907231D1/de not_active Expired - Lifetime
- 1999-12-06 BR BR9915996-1A patent/BR9915996A/pt not_active Application Discontinuation
- 1999-12-06 KR KR1020017007015A patent/KR20010082325A/ko not_active Withdrawn
- 1999-12-06 WO PCT/EP1999/009515 patent/WO2000034224A1/de not_active Ceased
- 1999-12-06 AT AT99963393T patent/ATE251110T1/de not_active IP Right Cessation
- 1999-12-06 ES ES99963393T patent/ES2211210T3/es not_active Expired - Lifetime
- 1999-12-06 CN CNB998159883A patent/CN100339355C/zh not_active Expired - Fee Related
- 1999-12-06 ID IDW00200101283A patent/ID29240A/id unknown
- 1999-12-06 US US09/856,461 patent/US6527932B1/en not_active Expired - Fee Related
- 1999-12-06 JP JP2000586674A patent/JP4233764B2/ja not_active Expired - Fee Related
- 1999-12-06 CA CA002353498A patent/CA2353498A1/en not_active Abandoned
-
2001
- 2001-06-05 MX MXPA01005629 patent/MX221393B/es not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US6527932B1 (en) | 2003-03-04 |
| JP2002531265A (ja) | 2002-09-24 |
| EP1137625A1 (de) | 2001-10-04 |
| MXPA01005629A (es) | 2001-08-01 |
| AU770841B2 (en) | 2004-03-04 |
| ES2211210T3 (es) | 2004-07-01 |
| WO2000034224A1 (de) | 2000-06-15 |
| DE19856376A1 (de) | 2000-06-08 |
| ID29240A (id) | 2001-08-16 |
| KR20010082325A (ko) | 2001-08-29 |
| ATE251110T1 (de) | 2003-10-15 |
| AU1970600A (en) | 2000-06-26 |
| EP1137625B1 (de) | 2003-10-01 |
| JP4233764B2 (ja) | 2009-03-04 |
| DE59907231D1 (de) | 2003-11-06 |
| CN1334796A (zh) | 2002-02-06 |
| MX221393B (en) | 2004-07-12 |
| CN100339355C (zh) | 2007-09-26 |
| BR9915996A (pt) | 2001-09-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |